US3513493A - Process for the coloring of materials based on cellulose acetate employing,as carrier,cyanoalkylation products - Google Patents
Process for the coloring of materials based on cellulose acetate employing,as carrier,cyanoalkylation products Download PDFInfo
- Publication number
- US3513493A US3513493A US671091A US3513493DA US3513493A US 3513493 A US3513493 A US 3513493A US 671091 A US671091 A US 671091A US 3513493D A US3513493D A US 3513493DA US 3513493 A US3513493 A US 3513493A
- Authority
- US
- United States
- Prior art keywords
- parts
- condensation product
- mole
- paste
- acrylonitrile
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/15—Locally discharging the dyes
- D06P5/155—Locally discharging the dyes with reductants
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
- D06L4/60—Optical bleaching or brightening
- D06L4/671—Optical brightening assistants, e.g. enhancers or boosters
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
- D06P1/6421—Compounds containing nitrile groups
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/36—Material containing ester groups using dispersed dyestuffs
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/921—Cellulose ester or ether
Definitions
- solvents, swelling agents or carriers such as for example glycols, phenylmethylcarbinol, acetic acid or its esters, acetins, urea, thiourea, formamide, dimethyl formamide, dimethyl sulp'hoxide, methyl-ethyl ketone, diacetone alcohol, -y-b-utyrolactone, dioxan, adiponitrile, nitrophenol, nitromethane, glycol-formal, methylene chloride, alkyl phthalates, glycol, salicylates, butyl benzoacetate, polyvinyl ethers, or zinc chloride.
- solvents, swelling agents or carriers such as for example glycols, phenylmethylcarbinol, acetic acid or its esters, acetins, urea, thiourea, formamide, dimethyl formamide, dimethyl sulp'hoxide, methyl-ethyl ketone, diacetone alcohol
- dyestuffs enable other classes of dyestuffs to be used, such as for example metalliferous complexes, acid dyestuffs, dyestuffs intended more particularly for dyeing polyester fibres, reactive dyestuffs, vat dyestuffs or fluorescent brightening agents.
- metalliferous complexes for example metalliferous complexes, acid dyestuffs, dyestuffs intended more particularly for dyeing polyester fibres, reactive dyestuffs, vat dyestuffs or fluorescent brightening agents.
- acid dyestuffs such as for example metalliferous complexes, acid dyestuffs, dyestuffs intended more particularly for dyeing polyester fibres, reactive dyestuffs, vat dyestuffs or fluorescent brightening agents.
- swelling agents or carriers may be mentioned: reduction of the brightness of the dyestuffs and of their yields; sublimation of the dyestuffs with a possible appearance of spreading around the printed patterns; precarious fixation of the dyestuffs, from which follows lack of fastness to wet tests; reduction in the dynamometric strength of the fibres; insufficient solubility or dispersiveness in water, which causes difficulty in removing them from the fabric by washing and defects in uni- 3,513,493 Patented May 26, 1970 ice formity; incompatibility with some thickeners, dispersing agents, surface-active agents or certain emulsions used in the printing pastes or the dyebaths; too great volatility, which causes loss of efficiency during thermal treatments.
- the present invention therefore has as its object an improvement in processes for printing, dyeing, discharging and optical bleaching of fabrics, threads, cards, films and other supports based on cellulose triacetate or cellulose diacetate.
- This new process is characterised by the fact that an acyclic compound containing at least one group, R and R' represent hydrogen atoms or CH:; groups, is used as a swelling agent or carrier.
- the catalyst may be, for example, an alkali metal or an oxide, hydroxide, alcoholate, hydride, cyanide or amide of an alkali metal.
- Quaternary ammonium hydroxides for example benzyltrirnethyl-ammonium hydroxide, or tertiary amines such as triethylamine, may also be used as catalysts if their basic character is sufficiently marked.
- the amount of catalyst to be used may vary from 0.01% to 5% of the weight of nitrile and the condensation temperature may vary within wide limits, preferably between the ambient temperature and the boiling temperature of the nitrile or the compound to be cyano-alkylated, and the reaction may be carried out under pressure.
- the carriers defined above may be used in proportions varying within wide limits. For example, for printing, 0.5% to 30% of the total weight of the printing paste, and for dyeing, 5 g. to 300 g. per litre, preferably 50 g. to 100 g. per litre of bath liquid may be used.
- materials based on cellulose diacetate or triacetate may be satisfactorily dyed or printed with plastosoluble dyestuffs, metalliferous complexes, dyestuffs intended more particularly for dyeing polyester fibres, vat dyestuffs, basic dyestuffs, acidic dyestuffs, reactive dyestuffs and fluorescent brightening agents, by incorporating compounds containing one or more groups in the printing paste or the dyebath.
- These carriers have swelling properties with respect to the fibre and solubilising properties with respect to the dyestuffs. They thus improve the diffusion of the molecules and conse quently the fixing of the dyestuffs.
- the acid dyestuffs could be fixed as easily and as firmly on fibres, such as for example cellulose acetate or triacetate, having an acid chracter and being slightly plastic.
- a printing paste is prepared containing the following ingredients:
- a printing paste is prepared containing the following ingredients 3 parts of 4-nitro (N-ethyl-N-hydroxyethyl) 4-aminoazobenzene 5 parts of the condensation product from one mole of glycerol and 2 moles of acrylonitrile 27 parts of water at 45 C. parts of a 13% carboxymethyl starch thickener 100 parts A triacetate fabric is printed with this paste. After drying, it is fixed by heat at 160 C. for 3 minutes, rinsed, washed and dried. A red shade with good fastness is thus obtained.
- a printing paste is prepared containing the following ingredients 8.0 parts of the dyestnff marketed as Esterophile Light Blue BLL paste (C.I. Disperse Blue 151) 5.0 parts of the condensation product from one mole of ethylene glycol and 2 moles of acrylonitrile 43.5 parts of water at 45 C.
- the dyestnff marketed as Esterophile Light Blue BLL paste (C.I. Disperse Blue 151) 5.0 parts of the condensation product from one mole of ethylene glycol and 2 moles of acrylonitrile 43.5 parts of water at 45 C.
- a blue shade is obtained with a tinctorial yield distinctly superior to that obtained under the same conditions in the absence of the condensation product or by replacing the emulsion by a 13% solution of carboxymethyl starch, and the condensation product by phenylmethylcarbinol.
- EXAMPLE 6 A printing paste is prepared containing the following ingredients:
- EXAMPLE 7 A printing paste is prepared containing the following ingredients:
- EXAMPLE 8 White discharge effects on a dyed dischargeable background may also be obtained.
- a printing paste is prepared containing the following ingredients:
- EXAMPLE 9 A printing paste is prepared containing the following ingredients.
- EXAMPLE 10 A printing paste is prepared containing the following ingredients:
- a dyebath for foularding is prepared composed of:
- EXAMPLE 12 A paste for Vigoureux printing is prepared containing the following ingredients:
- Vigoureux print is thus obtained of which the tinctorial yield is distinctly superior to that obtained in the absence of the above condensation product, or when it is replaced by parts of thiodiethylene glycol.
- EXAMPLE 13 A printing paste is prepared containing the following ingredients:
- EXAMPLE 14 A printing paste is prepared containing the following ingredients:
- EXAMPLE 18 A printing paste is prepared containing the following ingredients:
- the blue print previously obtained by the process of the invention has a tinctorial yield distinctly superior to those obtained on replacing the 8 parts of thiourea and the 16 parts of the above condensation product by 24 parts of N,N-bis-'(cyanoethyl)-formamide, or by 24 parts of thiourea, or by 24 parts of thiodiethylene glycol.
- EXAMPLE 19 A printing paste is prepared containing the following ingredients:
- a red shade is obtained with a tinctorial yield superior to that obtained on replacing the above condensation product by parts of thiodiethylene glycol.
- EXAMPLE 20 A printing paste is prepared containing the following components:
- EXAMPLE 21 A printing paste is prepared containing the following components:
- the condensate used may be prepared as follows:
- 920 parts of glycerol and 1.3 parts of sodium methylate are charged into a reactor provided with a stirring device, a thermometer, a reflux condenser and a bromine ampoule.
- the mixture is heated to C. and then 1060 parts of acrylonitrile are slowly run in over a period of 4 hours with the aid of the ampoule.
- the slightly exothermic reaction enables the temperature to be maintained at between 80 C. and C.
- the temperature is maintained for a further hour at 85 C.
- 2065 parts of a yellowish and oily product are obtained which is completely miscible with water, and the molecular weight of which is 197.5 and the hydroxyl value 290.
- EXAMPLE 22 A printing paste is prepared containing the following components:
- EXAMPLE 23 A printing paste is prepared containing the following components:
- EXAMPLE 24 A printing paste is prepared containing the following components:
- the condensate used may be prepared as follows: 9 parts of sodium methylate are dissolved in 732 parts of thiodiethylene glycol at 80 C. then 318 parts of acrylonitrile are run slowly in over a period of 50 minutes under a slight current of nitrogen while theztemperature is kept at 80 C. When the introduction is finished, the temperattire is maintained at 80 C. for a further 2 hours. After cooling and filtering, 900 parts of a crude product with an oily and yellowishappearance are obtained, which may be purified if desired so as to obtain the compound of the formula: Z
- a printing paste is prepared containing the following components:
- the bis-B-cyanoethoxy -diethyl sulphide can be prepared as follows: 7
- a printing paste is prepared containing the following components: V
- the condensate used can be prepared as follows: 10.5 parts of sodium methylate are dissolved in 742 parts of diethylene glycol at 80 C. then 371 parts of acrylonitrile are run slowly in at this temperature under a slight current of nitrogen in a period of one and a half hours. When the addition is finished, the mixture is maintained at 80 C. for a further 4 hours. After coolingand filtering, 1125 parts of a crude product with a yellowish and oily appearance are obtained which if desired may be purified in order to obtain the compound of the formula:
- a printing paste is prepared containing the following components:
- EXAMPLE 28 A printing paste is prepared containing the following components:
- a yellow shade is thus obtained of which the tinctorial yield is distinctly superior to that obtained, under the same conditions of fixation, in the absence of the above condensate.
- the colorations thus obtained have very good fastness to washing at 95 C. in the presence of soap and sodium carbonate, to degradation tests caused by acid or alkaline sweat and to gas fading.
- EXAMPLE 29 A printing paste is prepared containing the following components:
- the improvement which comprises the incorporation, as a carrier, of the product obtained by cyanoalkylating a compound containing at least one mobile hydrogen atom selected from the group and consisting of water, alcohols, polyols, oximes, hydrogen, sulfide, sodium sulfide, mercaptans, acetaldehyde and nitromethane with acylonitrile, u-methylacrylonitrile or crotonitrile.
- the carrier compound is an ingredient in a printing paste and is used in an amount of from 0.5 to 30% of the total weight of the paste.
- the carrier compound is the product resulting from the condensation of one molecule of glycerol with two moles of aclylonitrile.
- compositions for subjecting a material based on cellulose acetate to dyeing, printing, discharging or optical bleaching the improvement which comprises the incorporation, as a carrier, of the product obtained by cyanoalkylating a compound containing at least one mobile hydrogen atom selected from the group consisting of water, alcohols, polyols, oximes, hydrogen sulfide, sodium sulfide, mercaptans, acetaldehyde and nitromethane with acrylonitrile, a-methylacrylonitrile or crotoni- .trile.
- a compound containing at least one mobile hydrogen atom selected from the group consisting of water, alcohols, polyols, oximes, hydrogen sulfide, sodium sulfide, mercaptans, acetaldehyde and nitromethane with acrylonitrile, a-methylacrylonitrile or crotoni- .trile.
- composition according to claim 7 wherein the carrier compound is the product resulting from the condensation of one molecule of glycerol with two moles of acrylonitrile.
- composition according to claim 7 wherein the carrier compound is the product resulting from the condensation of one mole of Z-mercapto ethanol with one mole of acrylonitrile.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR27949A FR1474736A (fr) | 1965-08-11 | 1965-08-11 | Procédé de traitement des matières à base d'acétate de cellulose |
Publications (1)
Publication Number | Publication Date |
---|---|
US3513493A true US3513493A (en) | 1970-05-26 |
Family
ID=8586427
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US671091A Expired - Lifetime US3513493A (en) | 1965-08-11 | 1967-09-27 | Process for the coloring of materials based on cellulose acetate employing,as carrier,cyanoalkylation products |
Country Status (7)
Country | Link |
---|---|
US (1) | US3513493A (xx) |
JP (1) | JPS516264B1 (xx) |
BE (1) | BE683391A (xx) |
CH (2) | CH970966A4 (xx) |
FR (1) | FR1474736A (xx) |
GB (1) | GB1155787A (xx) |
NL (1) | NL139369B (xx) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4441885A (en) * | 1981-04-29 | 1984-04-10 | Ciba-Geigy Corporation | Anticrease finishing composition and use thereof in the dyeing or whitening of textile material which contains polyester fibres |
US4453946A (en) * | 1981-04-29 | 1984-06-12 | Ciba-Geigy Corporation | Dyeing assistant and use thereof in dyeing synthetic fibre material |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5016474B1 (xx) * | 1971-06-30 | 1975-06-13 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1398357A (en) * | 1919-10-31 | 1921-11-29 | American Cellulose | Dyeing fibers, threads, or fabrics |
US2518644A (en) * | 1947-04-16 | 1950-08-15 | Celanese Corp | Dyeing cellulose derivatives in the presence of inorganic thiocyanates and organic acids |
US3206274A (en) * | 1959-07-23 | 1965-09-14 | Celanese Corp | Processing of cellulose triacetate |
-
1965
- 1965-08-11 FR FR27949A patent/FR1474736A/fr not_active Expired
-
1966
- 1966-06-29 BE BE683391D patent/BE683391A/xx not_active IP Right Cessation
- 1966-07-05 CH CH970966D patent/CH970966A4/xx unknown
- 1966-07-05 CH CH970966A patent/CH523377A/fr not_active IP Right Cessation
- 1966-07-22 NL NL666610394A patent/NL139369B/xx not_active IP Right Cessation
- 1966-08-02 JP JP41050394A patent/JPS516264B1/ja active Pending
- 1966-08-11 GB GB35957/66A patent/GB1155787A/en not_active Expired
-
1967
- 1967-09-27 US US671091A patent/US3513493A/en not_active Expired - Lifetime
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1398357A (en) * | 1919-10-31 | 1921-11-29 | American Cellulose | Dyeing fibers, threads, or fabrics |
US2518644A (en) * | 1947-04-16 | 1950-08-15 | Celanese Corp | Dyeing cellulose derivatives in the presence of inorganic thiocyanates and organic acids |
US3206274A (en) * | 1959-07-23 | 1965-09-14 | Celanese Corp | Processing of cellulose triacetate |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4441885A (en) * | 1981-04-29 | 1984-04-10 | Ciba-Geigy Corporation | Anticrease finishing composition and use thereof in the dyeing or whitening of textile material which contains polyester fibres |
US4453946A (en) * | 1981-04-29 | 1984-06-12 | Ciba-Geigy Corporation | Dyeing assistant and use thereof in dyeing synthetic fibre material |
Also Published As
Publication number | Publication date |
---|---|
BE683391A (xx) | 1966-12-29 |
GB1155787A (en) | 1969-06-18 |
CH970966A4 (xx) | 1972-01-31 |
NL139369B (nl) | 1973-07-16 |
DE1619425A1 (de) | 1970-08-27 |
JPS516264B1 (xx) | 1976-02-26 |
CH523377A (fr) | 1972-01-31 |
FR1474736A (fr) | 1967-03-31 |
NL6610394A (xx) | 1967-02-13 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: PRODUITS CHIMIQUES UGINE KUKLMANN TOUR MANHATTAN L Free format text: CHANGE OF NAME;ASSIGNOR:CHARLES DAVENPORT;REEL/FRAME:004245/0711 Effective date: 19831116 |
|
AS | Assignment |
Owner name: PRODUITS CHIMIQUES UGINE KUHLMANN Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:PECHINERY UGINE KUHLMANN;REEL/FRAME:004319/0683 Effective date: 19840820 Owner name: PECHINEY UGINE KUHLMANN Free format text: MERGER;ASSIGNOR:UGINE KUHLMANN;REEL/FRAME:004319/0671 Effective date: 19840820 |